Simon's Sluts

Chapter One – Wake Up Call

The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my shapely calves, to sleek thighs and came to rest on the handcuff and curved tube chastity that encased my not insubstantial cock. I had been wearing it – except for daily supervised cleaning – for six days.

I sighed wistfully as I looked at the device. Before coming into Simon's service, I had been a daily – or twice or thrice daily – masturbator. Now, and for the last several months, I was only allowed to cum by Simon's leave – usually once a week, but sometimes not for twice that.

Turning from the mirror, I reached behind and gently extracted the medium butt plug that I wore at all times unless Simon specified something larger. Then I plopped down on the toilet for my morning pee and poop. After finishing, I prepared a warm, soapy enema and inserted the tube in my ass pussy. Gently squeezing, I took the entire bag into my twitching rectum. Then, straining not to leak a drop, I thoroughly cleaned and lubed the butt plug and re-inserted it.

With the relief of having help retaining the fluid sloshing around my bowels, I stepped into the shower and lathered from head to red-painted toe. I washed hair and body carefully and then shaved my already smooth legs and underarms. I carefully shaved as much pubic, scrotum and ass pussy as chastity and plug would allow. After months of twice-weekly electrolysis, I no longer needed to shave my face.

Stepping from the shower, I carefully removed the butt plug and sat on the commode to release the enema. The soapy water whooshed from my ass pussy sounding like a small waterfall. I cleaned my ass pussy carefully then lathered and shaved where the flanges of the plug had earlier prevented. Again, I cleaned and lubed the plug and re-inserted it. I then turned to hair and make-up. Since I was to be day maid today, the hair was easy. After blow drying, I simply piled it on my head and secured it with the white lace maid's headpiece. My makeup was slightly on the heavy side, but not too slutty; one of the other girls was today's slut.

Stepping into my closet, I carefully selected bra, corset, crotchless and backless panties and garter and hose. The bra, corset, panty and garter were all black and trimmed with frilly white lace. The stockings were fishnet, and accented with a tiny white bow on the top front of each leg. I put on the bra and inserted the expensive silicon pads Simon had provided to me. Over time, if things worked out, Simon would also provide top-quality implants.

I slipped into my garter belt and pulled the fishnets up my long, sleek legs and fastened them in place. Pulling the frilly panties up to my crotch, I thrilled at how sexy my constrained big clitty cock looked poking out of the open crotch. Looking over my shoulder and bending at the waist, I could see the flange of the butt plug framed by all that frilly white lace. I then stepped into five inch open-toe spiked sandals that showed of the bright red polish that matched both fingernails and lipstick. I walked to the intercom and pressed Vickie's button.

"Miss Vickie?" I said.

"Yes, Ellyce?" came the instant reply. Vickie, as head of the sluts, was usually up before the rest of the girls.

"Would you help me with final wash and corset, please?"

"Of course, dear", she replied. "I'll be there in a minute."

True to her word, Vickie entered within moments. Though in her mid-thirties, Vickie was the most amazing transsexual I had ever seen. In addition to stunning beauty, she had both grace and poise that the rest of us envied and to which we aspired. This morning, she was dressed in a chic silk business suit, the skirt of which came to mid-thigh. She would be Simon's secretary today, and I envied her since she would have the closest contact with him for the next ten hours or so.

She looked me over from head to toe and nodded her approval. "I believe Simon will be pleased with you today. You've come a long way. Come." With that, she led me back into my bath, and producing a handcuff key, removed the chastity. I knew better that to even think arousing thoughts; if Vickie had trouble getting the chastity back on because I had a hard on, I would be punished with additional duties, paddling and more. I quickly washed and shaved while Vickie cleaned and disinfected the chastity.

Back in my bedroom, I stepped into the loosely laced corset and tightened it as best I could. On my own, I probably achieved a twenty-four inch waistline. Vickie took over and when she was done, my waistline was a respectable twenty-two inches.

"Thank you, Miss Vickie," I said.

"You're welcome, dear." Though Vickie could be a strict disciplinarian, she was generally kind and giving. "You'd better hurry now. It's almost time for Simon to get up." She turned and left, and I went back to the closet and selected the ruffled slip and maid's uniform that would finish the outfit. I pulled on the many-layered slip, which poofed out and completely concealed and hint of my chastity-encased cock. I then donned the maid's uniform and tied the white apron tightly in place.

Leaving my room, I headed to the kitchen to prepare a light breakfast for Simon: eggs, buttered toast, coffee and orange juice. I placed Simon's breakfast on a silver breakfast tray and walked to Simon's master suite.

Opening the door, I walked across the enormous room, through the outer study/sitting room and into the bedroom proper. I placed the breakfast tray on a sideboard and went to rouse the bed slut, Tina. At some point during the night, she had kicked her blankets aside and as she slept there on her side, I could see lube and cum stains all over the back of her little nightie left over from Simon's passion. I stooped and lifted the stained short nightgown to make certain her plug and chastity were in place. Satisfied that I had no infraction to report, I roused her, sent her away – envious of the good fucking she'd had just hours before - and turned to my duties.

I stood quietly until the clock indicated seven and then pulled back the bedclothes to reveal Simon's magnificent body. At fifty, Simon was incredibly healthy and fit with the body of an athlete. His full head of hair was salt and pepper as was his bushy chest. I pulled the covers farther down to reveal Simon's salt and pepper pubis and his magnificent cock. His cock was not the biggest I have ever seen but it was certainly the most beautiful. Even lying there in it's flaccid state, it was easily six inches long and four around. When hard, it was easily eight and a half long by six around, and the big purple head was another inch around. His enormous balls hung heavy in a smooth-shaved scrotum.

I knelt on the bed and proceeded with my wake-up duties. I took Simon's beautiful dick in my mouth and began to gently suck. I could taste and smell the faint taste of Tina's ass pussy as I sucked and nursed on his wonderful cock. My own dick was straining painfully at my chastity, but the device was doing what it was designed for. He was quickly becoming hard and I moaned quietly his meat grew in my mouth, even though I knew it was unlikely I would be rewarded with his huge load; Simon rarely allowed himself to cum during his wake-up call.

Simon was fully awake now and making pleased noises. I glanced up and saw him smiling back at me. "That's good, Ellyce," he said. Your cocksucking gets better every day." All I could do was moan a little as I continued to suck. I knew that once he was fully hard, my treat would be taken away. Simon had only allowed me to eat his load a few times during wake-up, and he was usually in total control. Simon's cock was rock hard now and I could barley get my mouth around it. As expected, he pulled away from me and rolled out of bed.

I whimpered a little at being deprived of the object of my desire, which earned me a firm swat on my ass. "None of that, slut! You know the routine." Indeed I did. I moved to the edge of the bed on all fours and presented my ass to him. Simon lifted the uniform and petticoat to expose my plugged ass pussy. He eased the butt plug out of my ass pussy and presented it to my lips. Obediently, I opened my mouth and he inserted the plug down to the flange. I have to admit that the taste of my own ass pussy was intoxicating.

I tried to relax for what I knew was coming next. Simon was gentle but firm as he pressed the big purple head of his dick against the tight opening of my ass pussy. "That's it, Ellyce. Relax..... Spread for me." If not for the constant wearing of the butt plug, Simon's enormous cock would have torn me apart. As it was, I felt stretched to the limit as the head of Simon's dick penetrated my sphincter. I moaned as more and more of his massive tool penetrated me. The sensation rapidly passed from discomfort to pleasure and I moved back against him, my ass pussy now greedy to be filled and fucked. That earned me another firm swat, this time on the backless ruffled panties and I yelped in surprise and pain.

"Hold still, bitch!" And I held as still as I could as inch after beautiful inch of Simon's big dick penetrated me. Finally, his big cock was buried up to the hilt in my hungry ass pussy as I crouched on all fours like a bitch in heat. My cock struggled in vain against the chastity. Simon heaved a sigh and began to piss up my ass pussy. He had a piss hard on and I was his morning relief. I was always amazed by the amount his bladder held each morning I had day maid duty. He pissed and pissed for what seemed like an eternity and I felt his hot salty fluid filling my bowels as surely as my earlier enema had.

Finally, Simon drained the last drop of his piss into me and slowly withdrew his hard cock until only the massive head was still in me. "Turn your head." I complied and he took the butt plug from my mouth. As he pulled the big purple head out of my ass pussy, I did my best to clamp down so that not a drop of his piss would leak out. He pulled the last of his cock head out slowly and immediately began to re-insert the butt plug. After his big dick had been in me, the plug seemed very small and it went in easily and I clamped down, happy that I had not leaked a drop.

Simon spun me around, still on my hands and knees, and presented his softening cock to my mouth for cleaning. I took it into my mouth and savored the taste and smell of my pussy mingled with the salty tang of his morning urine. I licked and sucked his beautiful cock clean until he was satisfied at which point he again pulled it away. This time I managed not to whimper, but the disappointment must have shown on my face because he smiled and said, "Don't worry. There's time enough for that later."

"Thank you, Simon," I said. "It's my pleasure to serve." And I meant it!

Immediately, I scrambled to my feet, straightened my uniform and went to Simon's dressing room, retrieved his silk robe and helped him into it.

"Would you like your breakfast at the table or in bed, Simon?" I asked.

"Take it to the table, please, Ellyce. Then bring me the papers and tend to your other duties. I think I'll work from home today, so I won't need additional assistance getting dressed." Simon took a sip of his coffee and said, "Oh, Ellyce?"

"Yes Simon?"

He smiled and said, "You're getting better at your duties. I'm very happy with your progress."

"Thank you, Simon. I'm pleased you think so."

"Good. Starting immediately, I want you to start wearing a large butt plug day and night."

"Yes, Simon," I said, shaking inside a little.

"Good girl. Now get to work.

Next: Chapter Two – Morning Duties